[OH:1][CH2:2][C:3]1([CH2:8][OH:9])[CH2:5][CH:4]1[CH:6]=[CH2:7].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH2:19]>N1C=CC=CC=1.C1CCCCC1.CCOC(C)=O>[C:10]([O:1][CH2:2][C:3]1([CH2:8][O:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][CH:4]1[CH:6]=[CH2:7])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1A solution of 5.5 g (43 mmoles) of 1,1-bis(hydroxymethyl)-2-vinylcyclopropane in 40 ml of pyridine was cooled to 0° and 18.5 g (130 mmoles; 15.2 ml) of benzoyl chloride was added dropwise over 15 minutes. The mixture was stirred at 22° for 2 hours. TLC in cyclohexane-EtOAc (4:1) indicated that the reaction was complete. The reaction mixture was treated with 8 ml of water and stirred at 22° for 20 hours. It was concentrated to a residual oil and redissolved in 150 ml of EtOAc and washed with 50 ml of water, three 50-ml portions of 2N HCl, four 50 ml portions of saturated NaHCO3, dried (MgSO4), filtered and concentrated to give 11 g (75%) of the title compound, Rf cyclohexane-ethyl acetate (4:1) 0.7.
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